


Risky Business

by RedShirtEnsignRicky



Category: Supernatural
Genre: Angst, Demon Dean Winchester, Drinking, Drinking to Cope, Evil Crowley (Supernatural), F/M, Infidelity, Light BDSM, Light Bondage, Manipulative Crowley (Supernatural), Mark of Cain (Supernatural), Post-Demon Dean Winchester, Post-Mark of Cain (Supernatural), Reader-Insert, Shameless Smut, Smut, Vaginal Sex
Language: English
Status: Completed
Published: 2020-10-04
Updated: 2020-10-04
Packaged: 2021-03-08 00:08:25
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 7,420
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26806369
Author URL: https://archiveofourown.org/users/RedShirtEnsignRicky/pseuds/RedShirtEnsignRicky
Summary: You were deeply hurt by your boyfriend Dean when the Mark of Cain turned him into a demon. Crowley laments his lost bromance with the eldest Winchester. After having a few too many at the bar, you find yourself turning to Crowley for comfort. But any business with the King of Hell should come with a warning label. Will you come out of this unscathed?
Relationships: Crowley (Supernatural)/Original Female Character(s), Crowley (Supernatural)/You, Dean Winchester/Original Female Character(s), Dean Winchester/You
Comments: 2
Kudos: 36





	Risky Business

**Author's Note:**

> Hello All! This whole fic is basically an apology to Crowley for making him the bad guy that finishes last in the Lucifer fic I'm writing... but now I think a Dean apology fic is in order! Stay tuned for that soon!

“Don’t you think you’ve had enough?”

You glanced up at the bartender, a tall and lanky man with dusty brown hair, who was shaking his head at you.

“Not even close,” you replied darkly, taking another sip of your drink.

“Well, you’re done here,” he snipped back at you.

You rolled your eyes but didn’t argue. You _had_ been knocking back drink after drink for the better part of two hours, with no breaks or company to distract you. While you wouldn’t say you were totally wasted, there would definitely be a cab ride in order when you finally left. 

But what was to be expected? You were already dealing with enough – which is why you were at the bar in the first place – but this bartender had definitely made your mood even worse. He’d made a number of nasty little comments over the course of the evening. His barbs included not-so-subtle criticisms of your drinking, your outfit, and heavily implied that girls who came to bars alone were “only here for one thing.” You’d have already left, but this was the only bar in the tiny town where you and the Winchester brothers had stopped, and you _really_ needed a few drinks.

“Well, that’s no way to talk to a lady,” a heavily accented voice said quietly from behind. 

You turned your head and there stood the King of Hell himself.

_Holy crap!_ you immediately thought. Your heart leaped but you quashed your reaction. 

It wouldn’t do for anyone to know how Crowley affected you - especially Crowley himself. 

The bartender continued getting your bill together as if the demon were not there.

“May I join you, love?” Crowley asked you, but his eyes, slightly menacing, never left the rude bartender.

“Sure,” you answered, trying to appear indifferent to the idea. “But I’m about to get my walking papers here in a sec.”

True, Crowley had played something of a role in your heartache by gallivanting off with the demonic version of your boyfriend, but you didn’t hold it against him. Dean was the one who didn’t seem to have any intention of getting serious about you. He had been pushing you away ever since he’d gotten the mark from Cain. When he became a demon and you’d gone searching for him with Sam, he’d told you that you had meant nothing to him, even when he was human. He’d said you were “just another hunter skank” that he’d been hoping would give it up easy, but that there were hundreds more just like you.

Dean may have been a demon at the time he’d said it, but it still stung. And you were fearful that it was true. After all, he hadn’t exactly been quick to work on your relationship or even refute what he had said, even after he was cured.

After making himself comfortable onto the barstool next to you, Crowley leaned over towards you and asked, “Drowning your sorrows?” 

You chuckled without humor and replied, “Your demons spying on me?”

He smiled. “Perhaps. One does need to keep an eye on his friends, enemies, and threats to his throne.”

You turned your head to him, slightly amused in spite of yourself. “Really?”

“Ruling Hell 101, love,” he quipped.

“And which one of those categories do I fall into?” You questioned, narrowing your eyes.

He smirked widely, but didn’t answer.

The bartender returned and slapped the bill down in front of Crowley suddenly. 

“I see you found your company for tonight,” he said to you, smiling but there was not a trace of friendliness in his face. “I assume he’s taking care of your check and _seeing you safely home_.”

You glared at him and started to respond before Crowley stepped in.

“Beg your pardon?” he asked.

“You’re the inevitable pick up, right?” the bartender snidely commented. “Just so you know, she’s been searching the crowd for hours. Thought about taking her behind back myself at the end of the night, but she’s the stuck-up type, I can tell. Only interested in the one with the biggest wallet, no doubt, which is why she’s going for you. _I_ barely got a friendly word all night from the little-”

Crowley waved his hand to the back of the bar and a huge cloud of black smoke rushed from the area behind where you were seated, forcing itself down the bartender’s throat.

You gasped and glanced around. No one else in the bar seemed to have noticed; they were too wrapped up in their own fun.

Turning back, the bartender was looking at Crowley, but now his eyes were completely black.

“Crowley!” you whispered harshly.

“Oh, come now,” he replied placatingly. “I know you have your history with demons, and they with you. But you must admit, it’s an improvement.”

A loud sigh escaped your lips. 

_Well, he isn’t wrong,_ you thought to yourself.

“Besides,” he continued, waving the possessed bartender away. “Now we have more time to chat.”

Your brows furrowed together. 

“And why did you come to chat with me?” you asked, your voice dripping with suspicion.

Yeah, you secretly liked Crowley, but he was still _Crowley_.

He paused for a moment, before speaking.

“I thought perhaps you could do with some company who understands,” he said softly.

You snorted. “You?”

He angled his head challengingly. “Me.”

“And what would you know about having a boyfriend who treats you like crap?” you snapped.

Crowley smirked mysteriously and said, “Oh, you would be surprised, love.”

Your eyebrows raised in confusion. You didn’t know how to take that statement, but your imagination was racing. He didn’t elaborate.

“But I do know how it feels for your beloved Dean to totally turn his back on you. To treat you like his best mate one moment and then forget all about you the next,” he continued, his eyes drifting off and looking melancholy.

You weren’t buying it.

“Yeah, it must have been the worst moment of your sort-of life to have Dean refuse to kill for you and be another one of your toadies,” you replied, sarcasm laced with every word.

Crowley’s face dropped, before he turned to you, affronted.

“He was my best friend, not my toady,” he exclaimed. 

“Then why did you try to get him to kill people and do your dirty work?” you continued doggedly.

“Because it was what he _needed_ ,” Crowley contended. “Your beau was walking time bomb. It was only a matter of time before he dropped the curtain on someone. At least my way, it would have served a purpose and kept him from landing himself back on the FBI’s Most Wanted.”

“Yeah, you’re a giver,” you muttered.

He smiled. “Hardly. But I genuinely had good times with Dean. I was sorry to see it end, but he was becoming a detriment to my operation and my rule. I had no choice but to cut him loose.”

Crowley had that wispy look him his eyes when he was being halfway sincere, or at least since he had been injected with the holy blood.

Guilt wormed its way into you. You’d known there was something different about him since the failed attempt at the cure. There was a softness, a weakness of humanity, that had colored all of his actions since that fateful day. It must have been very hard for him, trying to walk that balance between ruling as the ruthless King of Hell and nurturing that tiny spark of humanity that he couldn’t seem to part with.

Then again, you had a certain affinity for Crowley that might be clouding your perception of him. Who knew?

You sighed, unsure what to think.

“Sorry,” you said quietly.

“Think nothing of it,” he replied, looking deeply at you.

And then there was an awkward silence. 

“I’m sort of surprised to find you in a place like this,” Crowley said to you, after a few moments.

You snorted. “Don’t tell me you’re going to pick up where he left off,” you said, your hand gesturing to the possessed bartender who was now making more drinks. 

“Pardon?” Crowley asked.

“With the misogyny,” you clarified.

“Hardly,” Crowley replied, smirking. “A true lady is a lady no matter where she is. It’s just that you don’t strike me as the kind of lady who just sits around enduring punishment. Maybe you’re more fun than I gave you credit for.”

You turned to him and stared in shock for a moment before a quick burst of laughter erupted from your mouth.

“I’m still with Dean, aren’t I? Haven’t you spied on us since he became human again?” you joked. “Or maybe you’re not as evil as I gave you credit for.”

Crowley chuckled, and scooted his stool a bit closer to you.

“I wouldn’t get too complacent, love, but you aren’t in any danger at the moment,” he assured you.

“Good to know,” you retorted, but there was no venom in your tone.

“Except maybe from your liver giving out,” he remarked, and your face darkened. Seeing this, he hastily added, “No judgement, of course. A true lady, remember?”

“You hung around with Dean all that time and you’re worried about _my_ liver?” you asked, sarcasm dripping from every word.

Where did he get off commenting on your life?

“Squirrel is a seasoned veteran in that area,” he replied easily. “Among others.”

Your face dropped at that implication. 

You knew Dean had quite a history with the ladies, but you generally tried not to think about it. You’d had no problem with it at all prior to the mark. If anything, you had been excited to see how amazing he would be when you finally slept together. Practice makes perfect, after all. 

But ever since he had taken the mark, Dean had been different. The confidence that you were all your boyfriend could think about had slowly withered as he drew further and further away from you.

“I’ve heard,” you replied shortly, insecurity bubbling in your belly. 

You had no desire to go further into that subject with Crowley.

“So, if you’re so bummed about Dean, why are you here instead of making up with him?” you asked, trying to shift the conversation back to Crowley.

“That ship has long since sailed,” Crowley answered. “And I’m interested to see if you are better company. Truthfully, Dean was a little wild for my taste.”

“But then, why are you _here_?” you repeated.

“To brighten you up, of course,” he said in response. “Put a smile back on that lovely face.”

He smiled at you so sincerely that you couldn’t help but feel a little flattered. And he thought you were lovely?

You felt a little tug in your chest at the thought of it.

Crowley had always been a dirty little secret of yours. True, he was evil and had been an enemy to you and your friends on many occasions. And yet, you still had always felt a weird kind of attraction to him. He wasn’t the tallest or handsomest, but he had an air of control and alpha to him that had drawn you to him. His brains were not unappealing either.

Not that you had ever let on about this to anyone. Dean and Sam would be livid.

“Good luck,” you said quietly. “But I would think a brilliant mind like yours would know a lost cause when you see one.”

“You are in a mood tonight, aren’t you?” he lamented. “I was hoping to hear more of that laugh.”

You chuckled. “I do appreciate the attempt to cheer me up; I just don’t think it’s going to work. Life kinda sucks right now,” you muttered.

“It’s not all bad; all things considered, you have a fairly decent life,” he said.

“Yeah, my boyfriend became a demon and pretty much forgot all about me. Yay for me,” you said unenthusiastically.

“It was the same way for me,” Crowley said earnestly. “Even if I’d had living friends or family, I wouldn’t have been looking them up after I got back to earth.”

“He didn’t forget about you,” you pointed out.

“Only because demons tend to hang out with demons. When you become a demon, you don’t much care for your human attachments anymore - they just aren’t any fun,” he said, but then held up his hands in a placating gesture. “It’s not personal, just a fact.”

“No offense, Crowley, but even if he was a demon, I find it insulting that he preferred you to me,” you grumbled.

“As if anyone could prefer anyone or anything to you,” he argued with a smile that made you squirm slightly.

You didn’t trust yourself to respond to a statement like that from Crowley. 

“Believe me, you weren’t missing anything. It was a lot more babysitting than mutual fun,” he told you, seeing that you were not reacting to his statement. At least not verbally. “I thought it would be so great - partnership, camaraderie, sharing everything. Maybe even you, if you had caught up to us before things went south.”

A little pulse went through you at the thought. Getting double teamed by both Dean and Crowley?

_Oh, God_ , you thought to yourself as your imagination went into overdrive.

“But, alas, it was not meant to be,” he said regretfully. 

“Well, I’m sorry your bromance didn’t work out,” you told him, sarcasm heavy in your tone but you were actually half-serious.

“Oh, I’m sure you are. We didn’t even get to the sharing you part. I guess I’ll always be the one that got away. Maybe I should be saying sorry to you,” he said, before taking a sip of his whiskey.

Your eyes widened before you burst into laughter, which made your cheeks and throat a little sore.

You hadn’t really laughed in months, you realized.

Maybe he was brightening you up, after all.

Time proved the King of Hell right. 

A few drinks later, Crowley actually had you howling hysterically by shamefacedly recounting his failures to reign Demon Dean in.

“And then,” he continued his tale of Dean, his accent becoming more pronounced as he drank. “He said I’d ‘have something fancy with your tiniest umbrella.”

A smirk curled across your lips before you responded, “Well, did you like it? The drink?”

“That’s beside the point,” he muttered indignantly.

Laughter erupted from your mouth.

“You had to know it wasn’t going to end well,” you teased. “Have you ever considered a different line of work? You don’t seem that bad, as far as demons go - no offense!”

You added this hastily upon seeing his insulted reaction, before continuing, “I’m just saying that maybe there’s something else out there that you could do, now that you aren’t under any other demons’ thumbs. I mean, you have to be getting tired of failing miserably on these ‘building a new Hell’ schemes…”

Crowley chuckled lightly at this. “You’re lucky you have your looks. Imagine talking to the King of Hell that way. I’d expect nothing less from Dean Winchester’s little love slave.”

You laughed together, but a little pang went through your heart at the mention of Dean.

“Well, now that I’ve ‘miserably failed’ again, and your beloved moron has been returned to you, you can go back to your wonderful romantic bliss. You really ought to be thanking me,” Crowley quipped.

Your mouth opened briefly as if you were going to respond, but you quickly closed it.

The demon did not miss this.

“What?”

“I don’t know if that’s going to be possible,” you said quietly.

“Why do you say that?” He asked, eyes probing yours.

You shifted in your seat uncomfortably for a moment, wondering if you should tell him.

Finally, you told him what had been on your mind when he arrived. “I’ve been thinking about back to (Y/Hometown),” you confessed. 

Crowley’s eyes widened. “Why?”

“Things… well, they haven’t been the same since he got the mark,” you said, before pouring your heart out to the demon king. “I’ve never loved anyone the way I love Dean, and I never doubted that he felt the same way up until he got the mark. His time as a demon made things worse, obviously, but he wasn’t my Dean even before that. He doesn’t smile, he doesn’t laugh with me. Honestly, I don’t think he’d even care if I went back home.”

“I’m sure that’s not true,” the demon king told you.

“I think it is,” you insisted.

“So, why are you telling me all of this and not Squirrel?” 

“I’ve tried, but he just doesn’t talk to me like he used to,” I said honestly. “I don’t know what to do.”

“Perhaps you just need to spend a little more time together to get things sorted out,” Crowley said.

You laughed humorlessly. “If Dean had time for me, would I be sitting here?” I asked him.

“Frankly, I don’t see why you are. I would think you would know better than to doubt his feelings for you,” he said.

“Easy for you to say. You’ve spent more time with him lately that I have,” I retorted.

“Maybe not as much as you think. Dean wasn’t spending his time with just me, if you recall,” Crowley pointed out.

Your face dropped as you remember Dean’s confession about the blonde girl he’d been seeing as a demon, and then you turned away to take sip of your drink.

He must have sensed your turmoil at his statement.

“Someone certainly has lovely pair of green eyes,” he said flippantly.

“Green eyes?... Oh,” you said, catching onto his meaning. “I’m not jealous.”

He tilted his head, a knowing expression overtaking his face.

“I’m not,” you insisted. “Dean wasn’t even really Dean when he knew...uh...”

You drifted off, as Dean had never shared the girl’s identity. He just told you she was ‘some blonde chick who I never intend to see again, so don’t worry about it.’ 

“I honestly can’t recall the little tart’s name,” Crowley told you. 

You laughed. “Good, because I don’t want to know it,” you said with a little giggle to cover up your unease.

“You find humor in this?” Crowley asked.

“Gotta laugh to keep from crying, right?” you answered. “Besides, it wasn’t Dean’s fault, obviously. Not the real Dean.”

Crowley let out a little snort, before draining the rest of his glass. “Well, you are the understanding sort, aren’t you?” he remarked.

You rolled your eyes. “It’s not like it’s worth ruining our whole relationship over a couple of kisses.”

You raised your glass to your lips and took another long sip, finishing another one.

“Kisses?” Crowley asked, his face drawn in confusion.

“Yeah, he told me all about his make out sessions with the blonde girl he’d been hanging out with,” you explained. “You aren’t breaking bro code, or anything. He came clean about it.”

He froze. “I see,” he said simply.

“It wasn’t exactly awesome to hear about it,” you went on. “But it wasn’t really him. And it was just a few kisses. How can I hold that against him after everything we’ve been through together?”

The demon king paused for a moment, looking as if he was weighing his options.

The pause got your attention immediately. “What is it?”

He didn’t answer immediately, contemplation etched into his face.

Then he spoke, slowly and deliberately.

“I’m afraid Dean may not have been… entirely forthright with you about his activities during that time,” he told you.

You froze. “What do you mean?” you asked, fear curling in your belly.

Crowley sighed sympathetically before continuing, “I’m truly sorry to be the one to have to tell you. Really, I am. But I’m afraid Dean and the blonde did a whole lot more than just kiss. They were spending the night together practically the entire time we were in that town. Once I even caught them in my bed. I don’t think it meant anything to him, then or now, but there you are.”

A huge weight was forming in your chest.

He had confirmed your worst fears.

Dean had lied to you. 

You could have forgiven him for sleeping with the blonde girl. Sure, it would have hurt. But it would not have kept you from welcoming him back when he regained his humanity. As you had already reasoned, the demon had not really been your Dean. His actions were not the actions of the sweet and brave hunter who had stolen your heart.

But this was different. He’d lied to you about it, and that was why you were now feeling the harsh sting of betrayal. How could he?

You sniffed, quickly raising your hand to cover a tear that escaped your eye.

Crowley pulled out a fancy black silk handkerchief from his suit jacket.

“Now, now,” he said consolingly, blotting your cheeks with the handkerchief as more of your tears rolled over them. “None of that.”

You let out a soft sob. “How could he do that?” you asked.

“You know he wasn’t himself, love,” he answered. 

“But why would he lie?” you continued angrily. Dean had fucked that blonde!

He sighed, pausing for a moment before replying. 

“I think he just wanted to spare your feelings, especially for something that he never would have done as himself,” Crowley reasoned.

At that moment, you weren’t too sure of that anymore.

The demon bartender returned, and set another drink in front of each of you.

You hastily fixed your expression.

There was no use sitting there crying about it. It’s not like you could question your boyfriend now, not while he was away finishing up his case. But the Winchesters were due to return in the morning. Dean was in for a very unpleasant day when you saw him tomorrow. 

“Thank you for being honest,” you told Crowley quietly.

The King of Hell smiled as his hand reached up to touch the soft skin of your back that was peeking through your shirt and pants.

“Don’t go ruining my reputation, love,” he told you jokingly.

“You are honest,” you giggled in spite of your miserable mood. 

“Am I now?” he questioned.

“Yes,” you insisted. “You always hold your contracts to the letter.”

His eyes were amused but searched yours for a moment. “One would think you consider me… well, almost _noble_ ,” he quipped.

“Well, maybe for a demon,” you told him, your tone playful but deep down, you kind of meant it. He was evil but he wasn’t evil like other demons you’d met.

“A noble demon,” Crowley murmured. “Is that why you’ve decided to grace me with your company tonight?”

“You came in here after me!” you laughed.

“Well, you’re the one who hasn’t gotten up and left,” he replied smoothly.

Your smile fell.

He had a point, after all. 

Crowley was supposed to be Winchesters’ enemy. Your enemy.

And yet, you were sitting here drinking with him. Acting like he was a friend. Crying on his shoulder. 

_Flirting_ , your subconscious scolded you. _When you have a boyfriend._

You quickly quashed that thought.

After all, what did it hurt if you flirted a little with Crowley? Dean had done a whole lot worse to you. A little harmless flirting, you rationalized to yourself, was not nearly enough to offset what he had done. 

_A little flirting, just for one night,_ you told yourself. 

You wouldn’t let it go any further.

“How about we just go back to chit chat?” you suggested.

“I wasn’t aware we’d ever left it, but have it your way,” he agreed.

You rolled your eyes. “This is your idea of chit chat? Kind of heavy, don’t you think?” 

“Oh, you couldn’t handle what I would consider ‘heavy,’” he stated.

He probably wasn’t wrong.

“How about we just play twenty questions?” You asked. 

That should be light and safe.

“And how do you play that?”

“We ask each other 20 questions,” you replied sarcastically.

He shuddered and looked away. “Oh, God...”

You smirked at the demon king.

“Don’t be a baby,” you teased.

Hi eyes cut back to you. “I ask first,” Crowley stipulated.

You raised an eyebrow, but nodded. “Fine.”

“First question,” Crowley asked, donning a serious face that made you wonder if this was a bad idea, after all. 

“What color knickers are you wearing?”

You gasped, but immediately began laughing again.

“Really, Crowley?” you jeered. “You have a golden opportunity to interrogate someone close to the Winchesters and this is what you ask?”

He smirked, looking very sexy to you.

“I want to know,” he persisted. “Believe me, it’s crucial information for my evil plans later tonight...”

Shaking your head, you told him.

“Ah, I’ve always thought you looked great in that color,” he said. 

“You’re such a comedian,” you said.

“Oh, I’m not joking,” he told you seriously.

You drew in a breath, feeling your face and chest heat up.

“Um, your favorite childhood memory?” You asked, trying to change the subject.

You didn’t need him seeing how he was affecting you.

“I don’t really have any good ones,” he told you. “You wouldn’t believe what I had for a mother.”

He rolled his eyes, looking annoyed at his own thoughts.

Then he continued.

“Your favorite restaurant?”

“Why would you want to know that?”

“Well, I’m personally having a good time tonight. You never know when we might want to get together again,” he said seductively.

You breathed deeply, trying to steady yourself. 

Seeing your reaction, the demon continued, “I’d be the envy of the town to have you on my arm.”

A mock frown crossed your face.

“Just the town?”

Crowley smirked.

“You’re beautiful enough to make me the envy of the universe, but we aren’t _that_ famous yet, love,” he quipped.

You laughed.

“Your turn,” he said. 

You thought about it for a moment, before choosing your question. 

“How about… the demon deal customer that you felt the least sorry for?” you asked.

Crowley looked thoughtful for a moment, before smiling.

“I would have to say a certain insurance salesman that I came across… oh, it must be going on twenty years ago now,” he recounted. “Imagine, insurance salesman lucks up. Meets the heiress. They fall for each other, have a great life. And then comes the mistress.”

“What a fucking prick,” you growled. This was not the kind of story you needed to hear tonight.

“What the poor bloke didn’t realize, though, is that his beloved mistress that he’d squandered all of his wife’s cash on was actually one of Lillith’s little whores. Some demons have a real love for money, you know,” he explained. “Not all of us are as noble as I am, I’m afraid. She cleaned him out. Left them both with nothing. But Lillith was all too happy to have me broker a deal for him. His wife had been welcomed back to her trust fund family with open arms while he was left with nothing. You could practically smell the desperation on him to be living the good life again.”

“He didn’t really deserve to have a boatload of cash, though, did he?” you said, scowling.

“Hence, he had to ante up his soul to get it back,” Crowley contended. “Sometimes, when you get yourself mixed up with a demon, there are serious consequences.”

He took a long look at you before taking another sip of his Craig.

“But, hey, he got his fortune back and a whole ten years to squander it,” he told me. “He didn’t have two pennies to rub together by the time he came to me, so I’m assuming those were ten years well enjoyed.”

You chuckled.

“Like I said, you’re a real giver.”

“I did make this lovely night possible, after all,” he said, raising his glass as if to toast himself.

“Really, you’re the one who should be grateful to me,” you teased.

“ _I_ should be grateful?” he asked, shocked.

“Yeah, you. I’m the one over here wrecking my liver to entertain you, not that you have to worry about that,” you quipped.

He frowned. “I’m making sacrifices, too,” he insisted with mock indignation. 

“How so?”

“I’m going to have so much paperwork waiting for me tomorrow morning,” Crowley lamented only half seriously. “I’d meant to knock out the majority tonight, but here I am, drinking with Y/N.”

You downed the last of your drink. “I suppose I should be flattered?” you laughed.

_I am_ , you thought to yourself.

“You _are_ getting over quite well tonight. You wouldn’t believe what some will offer up, just for a chance to spend a night with me,” he said softly, smiling but looking absolutely serious. “And I’m happy to oblige them.”

“As long as you get what you want in return?” you guessed. “Rough sex and an even rougher morning after?”

His dark chuckle was really growing on you.

“Among other things. I am a demon, after all,” he said, smirking. “But you didn’t ask for my company tonight, so I can’t charge you for it.”

You smiled, but it didn’t exactly resonate through you. You almost wished he was charging you rough sex… 

“Good to know.”

He returned your smile briefly before it faded away, replaced with something that caused a rush through your whole body.

“But I think you need a little more than just alcohol and some friendly banter to sooth you tonight, my dear,” he said.

There was no longer any levity in his voice.

The smile left your lips. Your breathing was picking up again.

Crowley moved closer to you again - close enough that you could feel his breath on your face.

“I could be persuaded to give you what you need,” he said, looking deeply into your eyes. “But it’s going to cost you, of course. You’ll have to give me what I want in return.”

_He does want sex!_ you gushed to yourself. 

You couldn’t have turned him down for anything.

“What is it that you think I need?” you asked him, pressing your thighs together.

There was only one thing you needed right now and you were desperately hoping that he needed it, too.

“You need to be desired,” he told you. “You need to be the only thing on my mind, the one I’d do anything to have. You’ve been playing second best for far too long. It’s time you came first to someone. Had me focused completely on you. Here. Now.”

“Yes,” you whispered, leaning towards him.

Crowley leaned towards you, brushing his lips and nose across the side of your face.

Then, abruptly, he leaned back into his stool, causing you to groan in protest.

“I’m not like that dog and pony show you call the Winchesters,” Crowley warned you with an arrogant smirk. “I’m an entirely different breed of animal.”

“You do know I never did anything with either of them, right?” you shot back with a smirk that was still, somehow, a little shy. “Not anything more than kissing, anyways.” 

“Now, now… don’t go making me feel special, love,” he replied before kissing your neck, adding a few nips to the sensitive flesh between kisses.

Your eyes fluttered shut as arousal shot through your entire body. You moaned before telling him insistently, “You’re special to me.”

He chuckled in your ear. “You’ll have to convince me,” his dark voice sounded.

You were determined to.

You opened your eyes and turned your head back to look at him. As you stared backwards into his dark eyes, you leaned your whole body back into him, pressing your form insistently against his. Your lips found his, kissing him deeply and desperately so he’d have no doubt of how much you wanted him.

Growling lightly, his voice rough, he returned your kiss but quickly started becoming dominant. His tongue found its way into your mouth, exploring deeply but never letting you get the upper hand. 

This continued a few more moment before he placed one of his hands firmly on your back between you, rubbing it sensually for a second before pressing hard, roughly pushing your body down to the bed.

_Bed?_ you thought to yourself.

You immediately stood up and looked around, but you were only able to because Crowley allowed it. He was bigger and stronger, even without taking his demonic abilities into consideration.

The two of you were no longer in the bar where you’d been drinking away your sorrows. 

Squinting your eyes, you attempted to take in your surrounds, but it was not easy. The room around the two of you was lavishly decorated, precisely the kind of place you’d expect to Crowley to stay – were he human and required sleep, that is. The bed he was pressing you back into was adorned with lavish silk black silk bedding, with a headboard of intricate carved and painted black wood. The high end furniture throughout the room was holding at least two dozen small candles, all lit but barely giving your human eyes any distinct visibility of much beyond them. You could make out that that walls of the room were a deep red with a black damask pattern decorated them, making the room seem even darker than it actually was. Beyond that, you were pretty much blind.

Crowley must have sensed your slight apprehension of your unfamiliar surroundings. “Second thoughts?” he asked. “It’s not too late to back out… yet.”

A deep feeling of unease was brewing in your belly, but not enough to make you turn back. You had promised to convince him, after all.

You answered him with another kiss, which he reciprocated for several minutes before, again, pushing you down to the bed. This time you ended up further towards the headboard. 

He was using his demonic abilities on you, it seemed. It was really turning you on.

Your hands brushed again something cool and hard. At the closer distance, you could make out a set of slim, antique black manacles that were attached by matching chains to the bed frame.

Crowley lay down on top of you, his larger frame pressing you into the cool sheets. You bucked your hips backwards into him, pressing your backside right against his hard cock.

He groaned and slinked his arm under your hips and pulled your lower half tighter against his.

“Last chance, Y/N,” he whispered in your ear, laving your neck with his tongue as he spoke. “If you don’t stop now, I’ll give you exactly what you want, but then you’ll have to give me what I want in return.”

“I want to give it to you,” you gasped. “I want to give it all to you!”

You felt his lips curve into a smile at that admission.

“Good, then I’ll take it,” he said.

Suddenly, your clothes were ripped into pieces and off of your body as if by magic.

You instinctively covered your breasts with your hands, and looked back. Crowley was still dressed in his usual immaculate attire. 

“What about you?” you asked, a trace of exasperation in your tone.

“Ah, ah, you’re giving everything to me,” he tells you. “And I get you in return.”

He flicked his wrists and you felt something cool caress my wrists before a click sounded.

You looked down and the manacles that had been lying up by the pillows were now locked securely around your wrists. However, the chains did not lead back to the bed. Instead, they merged into one single solid chain and manacle that was secured around Crowley’s right wrist.

“Now, I have you,” he said, shooting you an arrogant smirk.

“But you’re bound to me, too, aren’t you?” you shot back. 

“But you’re not dangerous to me, love,” he chided you with a smile. “And I can assure the reverse is most certainly not the case.”

He yanked his right wrist and pulled you forward onto your belly before him. 

“Open my trousers,” he ordered.  
  
Your fingers reached to the buckle of his belt, quickly unfastening it. You moved next to the button of his pant, which you quickly undid before lowering the zipper. Where you were expecting to encounter the silky black boxers, instead you found his bare skin. Apparently, Crowley likes to go commando.

“Pull out the little devil, Y/N,” he whispered, but it was no less an order.

You eagerly did as you were told. Reaching further into his pants, your hands found his hard cock that could hardly be categorized as “little” anything.

“Kiss it.”

You moved your lips to the head, kissing it softly before starting to slide his entire cock into your mouth.

Crowley yanked his chained wrist to the side, pulling you down to the bed on your belly again.

“Did I tell you to take me in your mouth?” He snapped.

“No,” you answered.

“No, _my lord_ ,” he corrected me.

“No, my lord,” you repeated dutifully. God this was so, so wrong but you were dripping in anticipation.

“A little punishment, I think,” he continued. “I did promise to give you what you need, after all.”

“I need to be punished?” you asked.

“Oh yes, pet, you’re taking a lot of liberties with my body,” he replied.

“Isn’t it kind of ironic for a demon possessing someone else to talk about taking liberties with other people’s bodies?” you shot back, unable to restrain yourself.

Crowley brought his hand down instant, swiftly delivering a series of smacks to the round flesh of your behind.

“Crowley!” you screamed and moaned simultaneously. 

You couldn’t believe how hot you were getting…

“That will be your punishment every time you open that smart mouth of yours without permission, or for any other transgressions on your part,” he told you quietly, but with absolute authority in his tone. “Do you understand?”

You continued breathing heavily, feeling your wetness starting to slide down the inside of your thighs.

He brought his hand down again, slapping your ass soundly.

“Do. You. Understand?!,” he snapped.

“Yes!”

He slapped your ass again.

“Yes, what?” he shouted.

“Yes, my lord!” you screamed.

He started rubbing your ass softly, soothing the reddened skin that was still smarting.

“Good girl, we’ll get you in line,” he said softly.

His fingers moved from your stinging rump down to the lips covering your entrance, stroking them teasingly and enticing several loud moans from your mouth.

“Oh, God…” you cried softly.

“Not exactly, love, but good to know I’m making such an impression,” he quipped. 

His fingers pushed against your wet entrance, slowly entering your cunt.

You shrieked before moaning in sync with his fingers moving in and out of your body.

“Do you like it, pet?” Crowley asked, a low growl discernible in his voice.

“Yes,” you moaned. 

“Am I giving you what you need?” He continued.

“Yes!” you cried out and pushed your hips backward, attempting to get more contact with him. 

“Just like I promised?” 

“Yes!”

“Better than Dean?”

“Dean?”

_Dean! Holy fuck, I’m cheating on Dean!_ you shouted to yourself internally.

Or were you?

Dean had done nothing but push you away ever since he got the mark. Even after it was removed, it was clear that he was just going through the motions of this relationship but not attempting to make it deeper. He didn’t even hit on you or try to talk you into his bed like he had every other female prior. Like he had with the blonde girl…

_That doesn’t make this right!_ you told yourself. _This is still cheating. It’s wrong, and if you do this, you’re going to have to suffer the consequences!_

You felt your legs being parted from behind and Crowley’s form shifting behind you, his hips pressing hard into your backside.

“I don’t know about you, love, but I’m eager to get down to business,” Crowley stated, and you felt him shifting around before something hard pressed against your pussy.

“I like screamers, so feel free to make a racket,” he joked.

Then he slammed into you, penetrating you with his hard cock all the way to your cervix on the first thrust.

Screamer, indeed.

You screamed like never before in your life. He was filling you to my limit and then some.

His demon deal, you recalled idly, had been to increase the size of his…

Did he choose this vessel because it was not lacking in…?

“Yes,” he groaned. 

He never paused to let you get used to him. He was immediately pulling out, granting you some very temporary relief before he shoved his cock right back into your pussy, and then again and again.

His hand pushed hard in the small of your back. “Arch your back more, love,” he ordered as he started to fuck you harder, moving against you at an increasing pace. “Lift that pretty little cunt up for me so I can wreck it.”

You eagerly did as you were told. Crowley increased the power of his strokes, slamming into your cervix with every thrust, making you cry out in pleasure and pain.

You pushed back as best as you could but could not move more than a few centimeters with his strong grip holding you firmly in place. 

You were a slave to him at that moment, unable to do anything but scream as he fucked you, taking everything he wanted.

And you loved every minute of it. You wanted to be his.

Suddenly, Crowley pulled his cock out of you completely and pulled away, ignoring your cries of protest. His hands grasped your hips and pulled, flipping you over to your back.

“You’re not close enough,” he complained, before wrenching your legs open and thrusting back into your pussy to the hilt in one stroke.

Holding your chained wrists down with his one, he started fucking you again, setting a brutal pace, intent on getting as far as he could inside you.

“Fuck, fuck,” you yelled, your weeping eyes rolling back into your head. “I’m coming!” 

Your pussy clenched him tightly, pulsating around his hard cock, eliciting a shout from Crowley. He grabbed your hips with his hands and thrust into you as hard and deep as he could, pounding you with so much strength that you were sure you were going to be injured. Your demon lover fucked you at this brutal pace for what felt like ages before coming undone, crying out your name a few times as he lost his rhythm. He groaned, thrusting erratically for a few more moments as he flooded your cunt with his cum.

Slowly, he collapsed onto your front, his still semi-hard cock lodged inside you.

“That was fantastic,” he groaned against you.

“Amazing,” you told him, breathing still returning to normal.

“I’m so going to enjoy this when I get to have you forever,” he whispered idly.

Your eyebrows scrunched together in confusion.

“What do you mean?” you asked.

He rose his head to look you in the eyes.

“When you come to me,” he told you, kissing your lips softly. “In ten years.”

You looked at him in shock, before pushing him off. 

Crowley chuckled, but allowed you to move his body off of yours. “A deal is a deal, love,” he insisted with confidence that made your belly go cold.

“But I didn’t make a deal with you!” you shouted, panic lacing your tone. “I would never sell my soul!”

“I specified that I would be expecting something in return, and you know perfectly well what I always demand as compensation for any services rendered. I am a _noble_ demon, after all,” he informed you. “And then you kissed me. I’m afraid that, however ambiguous, this deal is still binding. See for yourself.”

Crowley raised his hands and a burning sensation shot across your body’s surface. You looked down at yourself and red writing had appeared all over your body, scrawled across various large patches of your exposed skin.

“No!” you sobbed. This couldn’t be happening.

You desperately wanted to call Dean and beg for his help. But how could you?

“Yes, I’m afraid,” Crowley said heavily, but there was a hint of jest in his tone. “Prior knowledge of my demon deals is enough to ensure the contract’s validity, if you read the terms carefully. Your soul belongs to me now.”

“Well, give it back!” you demanded angrily, tears leaking copiously from your eyes.

His eyes traveled lewdly over your still nude form, before rising to meet yours with a dark chuckle from their owner. 

“Convince me.”

**Author's Note:**

> Thank you for reading! Feel free to come check out my page on tumblr as well! (redshirtensignricky)


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